43 Upcoming Races Near Winter Garden, FL - Matching: Trail Races

Sat, Nov 71 race

The Florida Run @ Lake Louisa State Park

Clermont, FL

Half, 10K, 5K

Sat, Nov 141 race

Run 4 Veterans

Dade City, FL

5K

Sun, Nov 151 race

Save the Manatee 5K

Orange City, FL

5K

Sat, Nov 212 races

5K with the 5-0

Oakland, FL

5K

The Sand Hill Adventure Run

Brooksville, FL

5K

Thu, Nov 261 race

Ultra Ultras Turkey Trot 5k

Lake Wales, FL

5K

Sat, Dec 51 race

CORE's 2026 Reindeer Run & Roll 5k

Altamonte Springs, FL

5K

Sat, Dec 123 races

AdventHealth Howey-in-the-Hills Reindeer Dash 5K presented by LiveTrends Design Group

Howey-in-the-Hills, FL

5K

Holly Jolly Jingle Bell Jog 5k

Lakeland, FL

5K

Sat, Dec 192 races

Santa's Run Fest

Winter Haven, FL

15K, 10K, 5K

Ancient Oaks 100-Mile Endurance Run

Titusville, FL

Ultra

Sun, Dec 271 race

Holiday Five (Five Days, Five Distances to choose from)

Winter Park, FL

Ultra, Marathon, Half

Sat, Jan 2, 20271 race

Florida Outlaw Ultra

Ocklawaha, FL

Ultra, Half

Sat, Jan 16, 20271 race

OUTLAST ORLANDO

Clermont, FL

Sat, Jan 23, 20271 race

DeBary 50K, Marathon, Half, 10K & 5K – MileBuilt Gemini Springs 2-Day Challenge

DeBary, FL

Ultra, Marathon, Half

Sat, Jan 30, 20272 races

Wild Florida 5K

Orlando, FL

5K

OUTLAST TAMPA

Lakeland, FL

Sat, Feb 6, 20271 race

The Hunt for Sasquatch

Mulberry, FL

10K, 5K, 1 Mile

Sun, Feb 7, 20271 race

AdventHealth Nighthawk Trail Run - Night Owl 5K and Coyote 10K

Lakeland, FL

15K, 10K, 5K

Sat, Feb 13, 20271 race

AdventHealth Lake Apopka Scenic Trail 30K Run, 8 Miler & 5K

Apopka, FL

Ultra, Half, 5K

Sun, Feb 14, 20271 race

Tracked Chair Adventures -- Run for the Woods

Sorrento, FL

5K

Sat, Feb 20, 20271 race

Winter Park 50K, Marathon, Half, 10K & 5K – MileBuilt Cady Way Bridge 2-Day Challenge

Winter Park, FL

Ultra, Marathon, Half

Sat, Feb 27, 20272 races

Running with the Herd 5k

The Villages, FL

5K

Inua 5k

Orlando, FL

5K

Sat, Mar 13, 20271 race

LSSC Shamrock Shuffle

Clermont, FL

1 Mile, 5K, 10K

Sat, Mar 20, 20271 race

The Spring Rising

Oviedo, FL

5K, 1 Mile, 10K

Sun, Mar 21, 20271 race

AdventHealth Lake Minneola Half Marathon, 10K and 5K

Clermont, FL

Half, 10K, 5K

Sat, Apr 3, 20272 races

Wekiva Parkway 5K

Apopka, FL

5K, 1 Mile

Cake by the Lake 5K Run and Walks

Inverness, FL

5K, 1 Mile

Sun, Apr 4, 20271 race

RUN YOUR BUNS OFF MARATHON @ RIDGE MANOR

Brooksville, FL

5K, 10K, Half

Sat, Apr 17, 20271 race

The Florida Run @ Colt Creek State Park

Lakeland, FL

Half, 10K, 5K

Sat, May 15, 20271 race

Stomp Out Suicide Trail Race

Dade City, FL

10K, 5K, 1 Mile

Sun, May 23, 20271 race

Sweat Swat n Swear

Inverness, FL

Ultra

Sat, May 29, 20271 race

Winter Park 50K, Marathon, Half, 10K & 5K – MileBuilt Cady Way Bridge Memorial Day 3-Day Challenge

Winter Park, FL

Ultra, Marathon, Half

Sun, Jun 13, 20271 race

AdventHealth Cool Sommer Mornings Triathlon-Duathlon-5K Series #1

Clermont, FL

5K, Ultra

Sat, Jun 19, 20271 race

The Florida Run LEFTOVER Trail Race

Clermont, FL

Sat, Jun 26, 20271 race

Independence Double (Two Days, Five Distances to choose from)

Winter Park, FL

5K, 10K, Half

Sun, Jul 11, 20271 race

AdventHealth Cool Sommer Mornings Triathlon\Duathlon\5K Series #2

Clermont, FL

5K, Ultra

Sun, Aug 8, 20271 race

AdventHealth Cool Sommer Mornings Triathlon\Duathlon\5K Series #3

Clermont, FL

5K, Ultra

Sat, Aug 21, 20271 race

Hot August Night Trail Race

Inverness, FL

Ultra, 10 Miles

Fri, Sep 3, 20271 race

DeBary 50K, Marathon, Half, 10K & 5K – MileBuilt Gemini Springs Labor Day 4-Day Challenge

DeBary, FL

Ultra, Marathon, Half

Sun, Sep 12, 20271 race

AdventHealth Cool Sommer Mornings Triathlon\Duathlon\5K Series #4

Clermont, FL

5K, Ultra